The Chetwynd passed by descent from the Chetwynds to the Peshalls, or Peshales, through the marriage of Joan of Chetwynd with Richard Peshall, prior to 1343, and devolved upon Joyce, the daughter of Richard Peshall. Joyce married Richard Pigott (d. 1439) and so took the Chetwynd Estate to the family that was to remain its owners until they sold the property in 1779. Three successive generations of the family served as High Sheriff – Robert in 1574, Thomas in 1615 and Walter in 1624 – and it is probable that this office would have stimulated improvements to the house at Chetwynd for each holder.

Royalists at the time of the Civil Wars, in the years following, ‘Thomas Piggott [sic.] of Chetwin, gent.’ is recorded as having been compounded for £440. Married to Ann, the daughter of Ralph Sneyd of Keele in Staffordshire, Thomas Pigott (d. 1665) had given hospitality to King Charles I at Chetwynd for three nights and, until the demolition of the gabled house, an oak-panelled room above the drawing room was revered as having been where the King had stayed. When he visited, Richard Symonds noted not only the adjacent church’s monuments and glass, but observed that ‘in the parlour windows of this pretty howse [sic.] of Mr. Pigott’s’ were displayed the arms of Pigott, Leveson, Corbet, ‘And many more’.

Thomas Pigott’s son, Walter (d. pre 1695) married as his second wife Anne, the fourth daughter of Sir John Dryden of Canons Ashby, Northamptonshire, a cousin of the poet Dryden. This was an alliance which brought the Chesterton Estate in Huntingdonshire to their son, Robert (1664–1746), who also succeeded his father as the master of Chetwynd. Robert Pigott, who married Francis, the daughter of the Hon. William Ward, was High Sheriff of Shropshire in 1697 and served as MP for Huntingdon in 1715–34 whilst based at Chesterton, which passed to him from his cousin Erasmus Dryden. He was a staunch Jacobite who was in Rome in 1720 when the Pretender is said to have given him his portrait in ivory.